I usually find sync problems to be PC issues. But given your list can you share ANYTHING that you think may work?
I have loved my iPod Classic for years, but it has finally broke. I'd love to get another, but honestly I am quite sick of all the syncing problems I've has since upgrading my iTunes, and am therefore looking to other things.
I would prefer something with a good amount of space (My library currently rests at about 20 GB, so 32+ would be nice). I also don't want a touchscreen, because I'm 99% sure I'd manage to break it, so that rules out basically all other iPods.
Other than that, I just want something basic. No wifi or anything like that. Video playing ability would be nice, but not having it isn't a deal-breaker. I do want something fairly tough and not oversized, because my music comes everywhere with me. Any suggestions?